CN105324720A - Resist underlayer film forming composition containing substituted crosslinkable compound - Google Patents

Resist underlayer film forming composition containing substituted crosslinkable compound Download PDF

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Publication number
CN105324720A
CN105324720A CN201480035763.8A CN201480035763A CN105324720A CN 105324720 A CN105324720 A CN 105324720A CN 201480035763 A CN201480035763 A CN 201480035763A CN 105324720 A CN105324720 A CN 105324720A
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lower membrane
resist lower
integer
formula
carbon number
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CN105324720B (en
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桥本圭祐
高濑显司
新城彻也
坂本力丸
远藤贵文
西卷裕和
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Nissan Chemical Corp
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Nissan Chemical Corp
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/10—Polyhydroxy benzenes; Alkylated derivatives thereof
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C43/14—Unsaturated ethers
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
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    • C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
    • C09D161/04—Condensation polymers of aldehydes or ketones with phenols only
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    • C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
    • C09D161/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C09D161/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/094—Multilayer resist systems, e.g. planarising layers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/40—Treatment after imagewise removal, e.g. baking
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/3105—After-treatment
    • H01L21/311—Etching the insulating layers by chemical or physical means
    • H01L21/31127—Etching organic layers
    • H01L21/31133—Etching organic layers by chemical means
    • H01L21/31138—Etching organic layers by chemical means by dry-etching
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    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
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    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/3105—After-treatment
    • H01L21/311—Etching the insulating layers by chemical or physical means
    • H01L21/31144—Etching the insulating layers by chemical or physical means using masks

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Abstract

[Problem] To provide: a resist underlayer film which is suppressed in generation of a sublimate and exhibits good embeddability when applied to a substrate having a hole pattern, while having high dry etching resistance, wiggling resistance, heat resistance and the like, and which is used for a lithography process; and a method for manufacturing a semiconductor device, which uses this resist underlayer film. [Solution] A resist underlayer film forming composition which contains a resin and a crosslinkable compound that is represented by formula (1) or formula (2). (In the formulae, Q1 represents a single bond or an m1-valent organic group; each of R1 and R4 represents an alkyl group with 2-10 carbon atoms or an alkyl group with 2-10 carbon atoms having an alkoxy group with 1-10 carbon atoms; each of R2 and R5 represents a hydrogen atom or a methyl group; and each of R3 and R6 represents an alkyl group with 1-10 carbon atoms or an aryl group with 6-40 carbon atoms.)

Description

Comprise the resist lower membrane formation composition of replaced cross-linked compound
Technical field
The present invention relates to semiconductor substrate and add effective photoetching resist lower membrane formation composition crosslinking catalyst and comprise the resist lower membrane formation composition of this crosslinking catalyst in man-hour, and employ the Resist patterns formation method of this resist lower membrane formation composition, and the manufacture method of semiconductor device.
Background technology
In the manufacture of semiconductor devices, microfabrication is carried out in the photoetching by employing photo-corrosion-resisting agent composition all the time.Above-mentioned microfabrication is following processing method: the film forming photo-corrosion-resisting agent composition on the processed substrates such as silicon wafer; the mask pattern of the pattern of semiconductor devices is had to carry out irradiation ultraviolet radiation isoreactivity light across description on the thin film; develop, the processed substrates such as silicon wafer are carried out by the photoresist pattern of gained the processing method of etch processes as diaphragm.But in recent years, the high integrationization progress of semiconductor devices, the active ray used is also from KrF excimer laser (248nm) to ArF excimer laser (193nm) short wavelengthization.Accompany therewith, active ray becomes large problem from the impact of the diffuse reflection of substrate, standing wave, be widely applied the method that the resist lower membrane being called as antireflection film (BottomAnti-ReflectiveCoating, BARC) is set between photoresist and processed substrate.
In addition, for the purpose of further microfabrication, the exploitation that active ray uses the photoetching technique of extreme ultraviolet (EUV, 13.5nm), electron beam (EB) has also been carried out.When EUV lithography, EB photoetching, generally do not occur, from the diffuse reflection of substrate, standing wave, therefore not need specific antireflection film, but as with the auxiliary film being improved as object of the resolution of Resist patterns, adaptation, start extensively research resist lower membrane.
In order to suppress mixing (mixing) of the resist of such photoresist and the resist lower membrane formed between processed substrate and upper strata institute lamination, generally after coating on processed substrate, be formed as through firing process the thermoset cross-linked film that do not mix with resist.
Usually, in resist lower membrane formation composition, in order to form such heat cured film, except as except the fluoropolymer resin of principal ingredient, be also combined with cross-linked compound (crosslinking chemical), for promoting the catalyzer (crosslinking catalyst) of cross-linking reaction.Particularly, as crosslinking catalyst, mainly use the thermal acid generator such as sulfoacid compound, carboxylic acid compound, sulphonic acid ester.
In recent years, in the photoetching process that semiconductor device manufactures, when using above-mentioned resist lower membrane formation composition to form resist lower membrane, the generation deriving from the distillation composition (sublimate) of the low molecular compounds such as above-mentioned fluoropolymer resin, crosslinking chemical, crosslinking catalyst when burning till becomes new problem.Worry that such sublimate is in semiconductor devices manufacturing process, adhere in film formation device, accumulate and in polluting device, they become the producing cause of defect (defect) etc. on wafer as foreign matter attachment.Therefore, require the new lower membrane composition proposing to suppress as far as possible such sublimate produced by resist lower membrane, also the research (for example, referring to patent documentation 1, patent documentation 2) of the resist lower membrane of the so low distillation physical property of display has been carried out.
In addition, in order to good imbedibility and few sublimate amount, disclose to use there is the technology (with reference to patent documentation 3) that the glycoluril system of butyl ether and melamine series etc. have the crosslinking chemical of atom N.
Further, the compound (with reference to patent documentation 4, patent documentation 5) that side chain has hydroxymethyl, methoxy, ethoxyl methyl, methoxy propoxy methyl etc. is disclosed.
Prior art document
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 2009-175436
Patent documentation 2: Japanese Unexamined Patent Publication 2010-237491
Patent documentation 3: International Publication 2008-143302 pamphlet
Patent documentation 4: No. 11-160860, Japanese Unexamined Patent Publication
Patent documentation 5: Japanese Unexamined Patent Publication 2003-122006
Summary of the invention
Invent problem to be solved
The invention provides and manufacturing the resist lower membrane formation composition used in the photoetching process of semiconductor device.
The generation that the invention provides a kind of sublimate is few, the resist lower membrane formation composition that when coating the substrate with sectional hole patterns, imbedibility is good.
For solving the method for problem
In the present invention, as the 1st viewpoint, be a kind of resist lower membrane formation composition, it comprises resin and following formula (1) or the cross-linked compound shown in formula (2),
In formula, Q 1represent the organic group of singly-bound or m1 valency, R 1and R 4the alkyl of the carbon number 2 ~ 10 of the alkyl representing carbon number 2 ~ 10 respectively or the alkoxy with carbon number 1 ~ 10, R 2and R 5represent hydrogen atom or methyl respectively, R 3and R 6represent the alkyl of carbon number 1 ~ 10 or the aryl of carbon number 6 ~ 40 respectively.
N1 represents the integer of 1≤n1≤3, and n2 represents the integer of 2≤n2≤5, and n3 represents the integer of 0≤n3≤3, and n4 represents the integer of 0≤n4≤3, and 3≤(n1+n2+n3+n4)≤6.
N5 represents the integer of 1≤n5≤3, and n6 represents the integer of 1≤n6≤4, and n7 represents the integer of 0≤n7≤3, and n8 represents the integer of 0≤n8≤3, and 2≤(n5+n6+n7+n8)≤5.M1 represents the integer of 2 ~ 10.
As the 2nd viewpoint, be the resist lower membrane formation composition described in the 1st viewpoint, Q 1for singly-bound, or for being selected from the organic group of the m1 valency in the chain alkyl of carbon number 1 ~ 10, the aromatic series base of carbon number 6 ~ 40 or their combination,
As the 3rd viewpoint, the 1st viewpoint or the resist lower membrane formation composition described in the 2nd viewpoint, above-mentioned formula (1) or the cross-linked compound shown in formula (2) are by the compound shown in following formula (3) or formula (4), obtain with the reaction containing the ether compound of hydroxyl or the alcohol of carbon number 2 ~ 10
In formula, Q 2represent the organic group of singly-bound or m2 valency.R 8, R 9, R 11and R 12represent hydrogen atom or methyl respectively, R 7and R 10represent the alkyl of carbon number 1 ~ 10 or the aryl of carbon number 6 ~ 40 respectively.
N9 represents the integer of 1≤n9≤3, and n10 represents the integer of 2≤n10≤5, and n11 represents the integer of 0≤n11≤3, and n12 represents the integer of 0≤n12≤3, and 3≤(n9+n10+n11+n12)≤6.
N13 represents the integer of 1≤n13≤3, and n14 represents the integer of 1≤n14≤4, and n15 represents the integer of 0≤n15≤3, and n16 represents the integer of 0≤n16≤3, and 2≤(n13+n14+n15+n16)≤5.M2 represents the integer of 2 ~ 10.
As the 4th viewpoint, it is the resist lower membrane formation composition described in the 3rd viewpoint, above-mentioned formula (3) or the compound shown in formula (4), to carry out in the presence of acid catalyst with the reaction containing the ether compound of hydroxyl or the alcohol of carbon number 2 ~ 10
As the 5th viewpoint, be the resist lower membrane formation composition described in the 4th viewpoint, acid catalyst is catalyzer spent ion exchange resin,
As the 6th viewpoint, be the resist lower membrane formation composition described in any one of the 3rd viewpoint ~ the 5th viewpoint, the ether compound containing hydroxyl is propylene glycol monomethyl ether or propylene glycol monoethyl,
As the 7th viewpoint, be the resist lower membrane formation composition described in any one of the 3rd viewpoint ~ the 5th viewpoint, the alcohol of carbon number 2 ~ 10 is ethanol, 1-propyl alcohol, 2-methyl isophthalic acid-propyl alcohol, butanols, 2-methyl cellosolve or cellosolvo,
As the 8th viewpoint, be the resist lower membrane formation composition described in any one of the 1st viewpoint ~ the 7th viewpoint, resin is novolac resin,
As the 9th viewpoint, be the resist lower membrane formation composition described in any one of the 1st viewpoint ~ the 8th viewpoint, it comprises crosslinking chemical further,
As the 10th viewpoint, be the resist lower membrane formation composition described in any one of the 1st viewpoint ~ the 9th viewpoint, it comprises acid and/or acid agent further,
As the 11st viewpoint, be a kind of resist lower membrane, it is undertaken burning till obtaining by being coated on semiconductor substrate by the resist lower membrane formation composition described in any one of the 1st viewpoint ~ the 10th viewpoint,
As the 12nd viewpoint, it is a kind of formation method of the Resist patterns for the manufacture of semiconductor, it comprises following operation: coated by the resist lower membrane formation composition described in any one of the 1st viewpoint ~ the 10th viewpoint and semiconductor substrate carries out burning till and forms the operation of resist lower membrane
As the 13rd viewpoint, be a kind of manufacture method of semiconductor device, it comprises following operation: the operation being formed resist lower membrane by the resist lower membrane formation composition described in any one of the 1st viewpoint ~ the 10th viewpoint on a semiconductor substrate; This resist lower membrane is formed the operation of resist film; The operation of Resist patterns is formed by the irradiation of light or electron beam and development; Pass through the operation that formed Resist patterns etches this resist lower membrane; And the operation of processing semiconductor substrate is carried out by the resist lower membrane be patterned,
As the 14th viewpoint, be a kind of manufacture method of semiconductor device, it comprises following operation: the operation being formed resist lower membrane by the resist lower membrane formation composition described in any one of the 1st viewpoint ~ the 10th viewpoint on a semiconductor substrate; This resist lower membrane is formed the operation of hard mask; Form the operation of resist film further on the hard mask; The operation of Resist patterns is formed by the irradiation of light or electron beam and development; Pass through the operation that formed Resist patterns carrys out etch hard mask; The operation of this resist lower membrane is etched by the hard mask be patterned; And the operation of processing semiconductor substrate is carried out by the resist lower membrane be patterned,
As the 15th viewpoint, be the manufacture method described in the 14th viewpoint, hard mask is formed by the coating of inorganics or the evaporation of inorganics, and
As the 16th viewpoint, be the compound shown in following formula (5),
In formula, Q 3represent isopropylidene, R 14the alkyl of the carbon number 2 ~ 10 of the alkyl representing carbon number 2 ~ 10 or the alkoxy with carbon number 1 ~ 10, R 15represent hydrogen atom or methyl, R 13represent the alkyl of carbon number 1 ~ 10 or the aryl of carbon number 6 ~ 40.
N17 represents the integer of 1≤n17≤3, and n18 represents the integer of 1≤n18≤4, and n19 represents the integer of 0≤n19≤3, and n20 represents the integer of 0≤n20≤3, and 2≤(n17+n18+n19+n20)≤5.
The effect of invention
The alkyl that cross-linked compound used in the present invention is chain alkyl by the moieties (low-molecular-weight alkyl such as such as methyl etc.) of alkoxy methyl being replaced as carbon number 2 ~ 10, have the carbon number 2 ~ 10 of the alkoxy of carbon number 1 ~ 10 and the cross-linked compound obtained.
When forming cross-linked structure at this replaced cross-linked compound and resin-bonded, be divided into the large compound of the molecular weight that is equivalent to abovementioned alkyl part from being detached into of departing from of cross-linked compound.Therefore thinking, when being coated on by the resist lower membrane formation composition comprising cross-linked compound of the present invention on substrate and heat, the composition of distillation can be reduced.Sublimate described above is attached in chamber, and it drops on reason substrate becoming coating defects.
Therefore, the generation of composition of the present invention by using above-mentioned replaced cross-linked compound can suppress coating defects.
In addition, by the moieties (low-molecular-weight alkyl such as such as methyl etc.) of alkoxy methyl is replaced as carbon number 2 ~ 10 chain alkyl, there is the alkyl of the carbon number 2 ~ 10 of the alkoxy of carbon number 1 ~ 10 and the cross-linking reaction of the cross-linked compound obtained and resin is carried out lentamente.Therefore, adjoint with the crosslinked three dimensional stress caused when the resist lower membrane formation composition comprising cross-linked compound of the present invention being coated on fine sectional hole patterns mobility be reduced in coating after temporarily do not occur.Therefore, the composition of the application of the invention, can fill resist lower membrane formation composition in sectional hole patterns very close to each otherly.
Accompanying drawing explanation
Fig. 1 is the NMR spectrum of 4 replacement of the TBOM-BP-BU obtained by synthesis example 3.
Fig. 2 is the NMR spectrum of 4 replacement of the TBOM-BIP-A obtained by synthesis example 4.
Fig. 3 is the NMR spectrum of 4 replacement of the TPOM-BIP-A obtained by synthesis example 5.
Fig. 4 is the NMR spectrum of 4 replacement of the TEOM-BIP-A obtained by synthesis example 6.
Fig. 5 is the NMR spectrum of 4 replacement of the TIBOM-BIP-A obtained by synthesis example 7.
Fig. 6 is the NMR spectrum of 4 replacement of the EGME-BIP-A obtained by synthesis example 8.
Fig. 7 is the NMR spectrum of 4 replacement of the EGEE-BIP-A obtained by synthesis example 9.
Fig. 8 is the NMR spectrum of 4 replacement of the PGME-BIP-A obtained by synthesis example 10.
Fig. 9 is the NMR spectrum of 4 replacement of the EGIPE-BIP-A obtained by synthesis example 11.
Embodiment
The present invention relates to the resist lower membrane formation composition comprising resin and formula (1) or the cross-linked compound shown in formula (2).
Above-mentioned resist lower membrane formation composition in the present invention generally comprises resin, formula (1) or the cross-linked compound shown in formula (2) and solvent.The adjuvant such as acid agent, surfactant can be comprised as required further.The solid constituent of said composition is 0.1 ~ 70 quality % or 0.1 ~ 60 quality %.Solid constituent is except containing of the whole compositions after desolventizing is proportional from resist lower membrane formation composition.Resin (polymkeric substance) can be contained with the ratio of 1 ~ 99.9 quality % or 50 ~ 99.9 quality % or 50 ~ 95 quality % or 50 ~ 90 quality % in solid constituent.
In addition, in solid constituent, the cross-linked compound shown in formula (1) or formula (2) can be contained with the ratio of 0.01 ~ 50 quality % or 0.01 ~ 40 quality % or 0.1 ~ 30 quality %.
The weight-average molecular weight of polymkeric substance used in the present invention is 600 ~ 1000000 or 600 ~ 200000.
In the cross-linked compound shown in formula used in the present invention (1) and formula (2), Q 1represent the organic group of singly-bound or m1 valency, R 1and R 4the alkyl of the carbon number 2 ~ 10 of the alkyl representing carbon number 2 ~ 10 respectively or the alkoxy with carbon number 1 ~ 10, R 2and R 5represent hydrogen atom or methyl respectively, R 3and R 6represent the alkyl of carbon number 1 ~ 10 or the aryl of carbon number 6 ~ 40 respectively.
N1 represents the integer of 1≤n1≤3, and n2 represents the integer of 2≤n2≤5, and n3 represents the integer of 0≤n3≤3, and n4 represents the integer of 0≤n4≤3, and 3≤(n1+n2+n3+n4)≤6.
N5 represents the integer of 1≤n5≤3, and n6 represents the integer of 1≤n6≤4, and n7 represents the integer of 0≤n7≤3, and n8 represents the integer of 0≤n8≤3, and 2≤(n5+n6+n7+n8)≤5.M1 represents the integer of 2 ~ 10.
Above-mentioned Q 1can be singly-bound, or can for being selected from the organic group of the m1 valency in the chain alkyl of carbon number 1 ~ 10, the aromatic series base of carbon number 6 ~ 40 or their combination.Here, chain alkyl can enumerate following alkyl.Aromatic series base can enumerate following aryl.
As the alkyl of carbon number 2 ~ 10, ethyl can be enumerated, n-pro-pyl, isopropyl, cyclopropyl, normal-butyl, isobutyl, sec-butyl, the tert-butyl group, cyclobutyl, 1-methyl-cyclopropyl, 2-methyl-cyclopropyl, n-pentyl, 1-methyl-normal-butyl, 2-methyl-normal-butyl, 3-methyl-normal-butyl, 1,1-dimethyl-n-propyl, 1,2-dimethyl-n-propyl, 2,2-dimethyl-n-propyl, 1-ethyl-n-pro-pyl, cyclopentyl, 1-methyl-cyclobutyl, 2-methyl-cyclobutyl, 3-methyl-cyclobutyl, 1,2-Dimethyl-cyclopropyl, 2,3-Dimethyl-cyclopropyl, 1-ethyl-cyclopropyl base, 2-ethyl-cyclopropyl base, n-hexyl, 1-methyl-n-pentyl, 2-methyl-n-pentyl, 3-methyl-n-pentyl, 4-methyl-n-pentyl, 1,1-dimethyl-normal-butyl, 1,2-dimethyl-normal-butyl, 1,3-dimethyl-normal-butyl, 2,2-dimethyl-normal-butyl, 2,3-dimethyl-normal-butyl, 3,3-dimethyl-normal-butyl, 1-ethyl-normal-butyl, 2-ethyl-normal-butyl, 1,1,2-trimethyl-n-propyl, 1,2,2-trimethyl-n-propyl, 1-ethyl-1-methyl-n-propyl, 1-Ethyl-2-Methyl-n-pro-pyl, cyclohexyl, 1-methyl-cyclopentyl, 2-methyl-cyclopentyl, 3-methyl-cyclopentyl, 1-ethyl-cyclobutyl, 2-ethyl-cyclobutyl, 3-ethyl-cyclobutyl, 1,2-dimethyl-cyclobutyl, 1,3-dimethyl-cyclobutyl, 2,2-dimethyl-cyclobutyl, 2,3-dimethyl-cyclobutyl, 2,4-dimethyl-cyclobutyl, 3,3-dimethyl-cyclobutyl, 1-n-pro-pyl-cyclopropyl, 2-n-pro-pyl-cyclopropyl, 1-isopropyl-cyclopropyl, 2-isopropyl-cyclopropyl, 1,2,2-trimethyl-cyclopropyl, 1,2,3-trimethyl-cyclopropyl, 2,2,3-trimethyl-cyclopropyl, 1-Ethyl-2-Methyl-cyclopropyl, 2-ethyl-1-methyl-cyclopropyl, 2-Ethyl-2-Methyl-cyclopropyl and 2-ethyl-3-methyl-cyclopropyl etc.
In addition, about the alkyl of carbon number 1 ~ 10, except the alkyl of above-mentioned carbon number 2 ~ 10, methyl can be illustrated further.
As the alkoxy of carbon number 1 ~ 10, methoxyl can be enumerated, ethoxy, positive propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, 1-methyl-n-butoxy, 2-methyl-n-butoxy, 3-methyl-n-butoxy, 1, 1-dimethyl-positive propoxy, 1, 2-dimethyl-positive propoxy, 2, 2-dimethyl-positive propoxy, 1-ethyl-positive propoxy, just own oxygen base, 1-methyl-n-pentyloxy, 2-methyl-n-pentyloxy, 3-methyl-n-pentyloxy, 4-methyl-n-pentyloxy, 1, 1-dimethyl-n-butoxy, 1, 2-dimethyl-n-butoxy, 1, 3-dimethyl-n-butoxy, 2, 2-dimethyl-n-butoxy, 2, 3-dimethyl-n-butoxy, 3, 3-dimethyl-n-butoxy, 1-ethyl-n-butoxy, 2-ethyl-n-butoxy, 1, 1, 2-trimethyl-n-propoxy, 1, 2, 2,-trimethyl-n-propoxy, 1-ethyl-1-methyl-positive propoxy and 1-Ethyl-2-Methyl-positive propoxy etc.
As the aryl of carbon number 6 ~ 40, phenyl, naphthyl, anthryl etc. can be enumerated.
Above-mentioned formula (1) or the cross-linked compound shown in formula (2) can by make the compound shown in formula (3) or formula (4), with the reaction containing the ether compound of hydroxyl or the alcohol of carbon number 2 ~ 10 and obtaining.
Will to the compound 1 mole shown in formula (3) or formula (4), the formula (1) that the alcohol of the ether compound containing hydroxyl or carbon number 2 ~ 10 is replaced with the ratio of 1 mole and obtained or the compound shown in formula (2) are set to 1 replacement, the formula (1) similarly 2 moles of displacements obtained or the compound shown in formula (2) are set to 2 replacement, the formula (1) similarly 3 moles of displacements obtained or the compound shown in formula (2) are set to 3 replacement, the formula (1) similarly 4 moles of displacements obtained or the compound shown in formula (2) are set to 4 replacement.
In formula (3) and formula (4), Q 2represent the organic group of singly-bound or m2 valency.That is, above-mentioned Q 2can be singly-bound, or can for being selected from the organic group of the m2 valency in the chain alkyl of carbon number 1 ~ 10, the aromatic series base of carbon number 6 ~ 40 or their combination.Here, chain alkyl can enumerate abovementioned alkyl.Aromatic series base can enumerate above-mentioned aryl.
R 8, R 9, R 11and R 12represent hydrogen atom or methyl respectively, R 7and R 10represent the alkyl of carbon number 1 ~ 10 or the aryl of carbon number 6 ~ 40 respectively.
N9 represents the integer of 1≤n9≤3, and n10 represents the integer of 2≤n10≤5, and n11 represents the integer of 0≤n11≤3, and n12 represents the integer of 0≤n12≤3, and 3≤(n9+n10+n11+n12)≤6.
N13 represents the integer of 1≤n13≤3, and n14 represents the integer of 1≤n14≤4, and n15 represents the integer of 0≤n15≤3, and n16 represents the integer of 0≤n16≤3, and 2≤(n13+n14+n15+n16)≤5.M2 represents the integer of 2 ~ 10.
Formula (3) or the compound shown in formula (4), to carry out in the presence of acid catalyst with the reaction containing the ether compound of hydroxyl or the alcohol of carbon number 2 ~ 10.
Here used acid catalyst can use such as, p-toluenesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid pyridine , salicylic acid, 5-sulphosalicylic acid, 4-phenolsulfonic acid, camphorsulfonic acid, 4-chlorobenzenesulfonic acid, benzenedisulfonic acid, 1-naphthalene sulfonic aicd, citric acid, benzoic acid, hydroxybenzoic acid, the acid compound such as naphthoic acid.
But, in order to make the not remaining unreacted acid of reaction system, catalyzer spent ion exchange resin can be used.Catalyzer spent ion exchange resin can use such as, the strong acid ion exchange resin of sulfonic acid type.
The above-mentioned ether compound containing hydroxyl can enumerate propylene glycol monomethyl ether or propylene glycol monoethyl.
In addition, the alcohol of carbon number 2 ~ 10 can enumerate ethanol, 1-propyl alcohol, 2-methyl isophthalic acid-propyl alcohol, butanols, 2-methyl cellosolve or cellosolvo.
Cross-linked compound shown in formula used in the present invention (1) and formula (2) such as can be illustrated in following.
In addition, the compound shown in formula used in the present invention (3) and formula (4) such as can be illustrated in following.
As long as resin used in the present invention can form the resin of cross-linking reaction with above-mentioned cross-linked compound, just can use.Be cross-linked to form group as what exist in resin, hydroxyl, carboxyl, amino, alkoxy can be enumerated.
There are these resins being cross-linked to form group and can enumerate acrylic resin, novolac resin, preferably can use novolac resin.
Above-mentioned novolac resin is by carrying out reacting in the presence of acid catalyst obtaining by the compound containing aromatic rings and aldehydes or ketones compound.As the compound containing aromatic rings, such as benzene, phenol, naphthalene, phloroglucin, hydroxyl naphthalene, fluorenes, carbazole, bis-phenol, bisphenol S, diphenylamine, triphenylamine, nonox, anthracene, hydroxyl anthracene, phenothiazine, fen can be enumerated piperazine, Phenylindole, polyphenol etc.
In addition, as aldehyde, formaldehyde can be enumerated, paraformaldehyde, acetaldehyde, propionic aldehyde, butyraldehyde, iso-butyraldehyde, valeral, hexanal (カ プ ロ Application ア Le デ ヒ De), 2 methyl butyraldehyde, hexanal (ヘ キ シ Le ア Le デ ヒ De), the hendecanal, 7-methoxyl-3, 7-dimethyl octanal, hexamethylene aldehyde, 3-methyl-2-butyraldehyde, glyoxal, MDA, butanedial, glutaraldehyde, the representative examples of saturated aliphatic aldehydes such as hexandial, acryl aldehyde, the unsaturated aliphatic aldehydes such as methacrolein, furfural, the hetero ring type aldehydes such as pyridine aldehydes, benzaldehyde, naphthaldehyde, anthraldehyde, formaldehyde, salicylide, ethylalbenzene, 3-hydrocinnamicaldehyde, tolyl aldehyde, (N, N-dimethylamino) benzaldehyde, acetoxyl group benzaldehyde, the aromatic series aldehydes etc. such as 1-pyrene formaldehyde.
In addition, as ketone, be diaryl ketone, such as diphenylketone, phenyl napthyl ketone, dinaphthyl ketone, phenyltoluene base ketone, xylyl ketone, 9-Fluorenone etc. can be enumerated.
Novolac resin used in the present invention is the resin that the compound containing aromatic rings and aldehydes or ketone condensation are obtained.In this condensation reaction can relative to the aromatics containing heterocyclic radical comprise and participate in phenyl 1 equivalent that reacts, use aldehydes or ketone with the ratio of 0.1 ~ 10 equivalent.
As the acid catalyst used in above-mentioned condensation reaction, the carboxylic acidss such as organic sulfonic acid class, formic acid, oxalic acid such as the inorganic acids such as such as sulfuric acid, phosphoric acid, perchloric acid, p-toluenesulfonic acid, p-toluenesulfonic acid monohydrate can be used.The use amount of acid catalyst carries out various selection according to the kind of used acids.Usually relative to 100 mass parts of the compound containing aromatic rings, be 0.001 ~ 10000 mass parts, be preferably 0.01 ~ 1000 mass parts, be more preferably 0.1 ~ 100 mass parts.
Also can carry out even if above-mentioned condensation reaction is solvent-free, but usually use solvent to carry out.As solvent, only otherwise hinder reaction, just all can use.Such as tetrahydrofuran, two can be enumerated the ring-type ethers such as alkane.In addition, if the acid catalyst the used aqueous material that to be such as formic acid such, then the effect as solvent can also be had concurrently.
Temperature of reaction during condensation is generally 40 DEG C ~ 200 DEG C.Reaction time carries out various selection according to temperature of reaction, is generally 30 minutes ~ 50 hours.
In the present invention as the catalyzer of the cross-linking reaction for promoting the cross-linked compound shown in resin and formula (1) or formula (2), can by p-toluenesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid pyridine , salicylic acid, 5-sulphosalicylic acid, 4-phenolsulfonic acid, camphorsulfonic acid, 4-chlorobenzenesulfonic acid, benzenedisulfonic acid, 1-naphthalene sulfonic aicd, citric acid, benzoic acid, hydroxybenzoic acid, the acid compound and/or 2 such as naphthoic acid, 4, thermal acid generator or two (4-tert-butyl-phenyl) iodine such as 4,6-tetrabromo cyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylat, other organic sulfonic acid Arrcostab fluoroform sulphonate, triphenylsulfonium triflate sulfonate etc. the sulfonic acid system such as series of compounds photoacid generator class, benzoin tosylate, the N-hydroxy-succinamide triflate photoacid generator class etc. containing halogen such as salt system photoacid generator class, phenyl-bis-(trichloromethyl)-s-triazine carries out combining to coordinate.Cross-linking catalyst dosage is 0.0001 ~ 20 quality % relative to all solids composition, is preferably 0.0005 ~ 10 quality %, more preferably 0.01 ~ 3 quality %.
In photoetching resist lower membrane formation composition of the present invention, except mentioned component, optical absorbing agent, rheology control agent, bonding assistant, surfactant etc. can be added as required further.
In addition, the crosslinking chemical beyond formula (1), the crosslinker compound shown in formula (2) can be contained further.As this crosslinking chemical, melamine series, substituted urea system or their polymer system etc. can be enumerated.Preferably having at least 2 and be cross-linked to form substituent crosslinking chemical, is the compounds such as methoxymethylated glycoluril, butoxymethyl glycoluril, methoxymethylated melamine, butoxymethyl melamine, methoxymethylated benzoguanamine, butoxymethyl benzoguanamine, methoxymethylated urea, butoxymethyl urea, methoxymethylated thiocarbamide or methoxymethylated thiocarbamide.In addition, the condensation product of these compounds also can use.
As further optical absorbing agent, can be applicable to using such as, " industrial pigment Ji Intraoperative と city Games (technology and market of industrial pigment) " (CMC publication), commercially available optical absorbing agent described in " dyestuff Bian list (dyestuff brief guide) " (Synthetic Organic Chemistry association volume), such as, C.I. disperse yellow 1,3,4,5,7,8,13,23,31,49,50,51,54,60,64,66,68,79,82,88,90,93,102,114 and 124; C.I. disperse orange 1,5,13,25,29,30,31,44,57,72 and 73; C.I. Red-1 200,5,7,13,17,19,43,50,54,58,65,72,73,88,117,137,143,199 and 210; C.I. disperse violet 43; C.I. disperse blue 96; C.I. fluorescer 112,135 and 163; C.I. solvent orange 2 and 45; C.I. solvent red 1,3,8,23,24,25,27 and 49; C.I. naphthol green 10; C.I. pigment brown 2 etc.Above-mentioned optical absorbing agent is below 10 quality % with all solids composition relative to photoetching resist lower membrane formation composition usually, and the ratio being preferably below 5 quality % coordinates.
Rheology control agent, mainly in order to improve the mobility of resist lower membrane formation composition, particularly improving the film thickness uniformity of resist lower membrane, raising resist lower membrane formation composition adds in the object of the fillibility of inside, hole in roasting procedure.As concrete example, repefral can be enumerated, diethyl phthalate, diisobutyl phthalate, dihexylphthalate, the phthalic acid derivatives such as butyliso decyl phthalate, Di-n-butyl Adipate, diisobutyl adipate, diisooctyl adipate, the hexane diacid derivants such as hexane diacid octyl-decyl ester, n-butyl maleate, diethyl maleate, the maleic acid derivatives such as dinonyl maleate, methyl oleate, butyl oleate, the oleic acid derivatives such as tetrahydrofurfuryl oleate, or n-butyl stearate, the stearic acic derivatives such as tristerin.These rheology control agents coordinate with the ratio being usually less than 30 quality % relative to all solids composition of photoetching resist lower membrane formation composition.
Bonding assistant mainly in order to improve the adaptation of substrate or resist and resist lower membrane formation composition, particularly in order to avoid in development resist peel off and add.As concrete example, trimethyl chlorosilane can be enumerated, dimethyl vinyl chlorosilane, methyldiphenyl base chlorosilane, the chlorosilane such as CMDMCS chloromethyl dimethyl chlorosilane, trimethylmethoxysilane, dimethyldiethoxysilane, methyl dimethoxysilane, Vinyldimethylethoxysilane, dimethoxydiphenylsilane, the alkoxyl silicone alkanes such as phenyl triethoxysilane, hexamethyldisilazane, N, N '-bis-(trimethyl silyl) urea, dimethyl trimethyl silyl amine, the silazane classes such as trimethyl-silyl-imidazole, vinyl trichlorosilane, γ-r-chloropropyl trimethoxyl silane, γ aminopropyltriethoxy silane, the silanes such as γ-glycidoxypropyltrime,hoxysilane, benzotriazole, benzimidazole, indazole, imidazoles, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-sulfydryl benzo urea or the thiourea compounds such as the hetero ring type compounds such as azoles, urazole, thiouracil, mercaptoimidazole, mercaptopyrimidine, 1,1-dimethyl urea, 1,3-dimethyl urea.Relative to all solids composition of photoetching with resist lower membrane formation composition, usually to be less than 5 quality %, the ratio being preferably less than 2 quality % coordinates these bonding assistants.
In order to not produce pin hole, striped etc., improve the coating to uneven surface further, can matching surface activating agent in photoetching resist lower membrane formation composition of the present invention.As surfactant, such as polyoxyethylene lauryl ether can be enumerated, polyoxyethylene stearyl base ether, polyoxyethylene cetyl base ether, the polyoxyethylene alkyl ether classes such as polyoxyethylene oleyl ether, polyoxethylene octylphenyl phenol ether, the polyoxyethylene alkylaryl ether classes such as polyoxyethylene nonylphenol ether, polyox-yethylene-polyoxypropylene block copolymer class, sorbitan monolaurate, sorbitan-monopalmityl ester, sorbitan monosterate, dehydrating sorbitol monooleate, anhydrosorbitol trioleate, the sorbitan fatty ester classes such as anhydrosorbitol tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, the nonionic system surfactants such as polyoxyethylene sorbitan fatty acid ester such as polyoxyethylene sorbitan tristearate, エ Off ト Star プ EF301, EF303, EF352 ((strain) ト ー ケ system プ ロ ダ Network Star system, trade name), メ ガ Off ァ ッ Network F171, F173, R-30 (large Japanese イ Application キ (strain) system, trade name), Off ロ ラ ー De FC430, FC431 (Sumitomo ス リ ー エ system (strain) is made, trade name), ア サ ヒ ガ ー De AG710, サ ー Off ロ Application S-382, SC101, SC102, SC103, SC104, SC105, the fluorine system surfactants such as SC106 (Asahi Glass (strain) is made, trade name), organic siloxane polymer KP341 (SHIN-ETSU HANTOTAI's chemical industry (strain) system) etc.The use level of these surfactants is generally below 2.0 quality % relative to all solids composition of photoetching resist lower membrane formation composition of the present invention, is preferably below 1.0 quality %.These surfactants can add separately, also can two or more combination add in addition.
In resist lower membrane formation composition of the present invention, as making above-mentioned resin and crosslinker component, the solvent that crosslinking catalyst etc. dissolve, ethylene glycol monomethyl ether can be used, ethylene glycol monomethyl ether, methylcellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, carbiphene, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl, propylene glycol monoethyl acetic acid esters, propylene glycol propyl ether acetic acid esters, toluene, dimethylbenzene, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2 hydroxy propanoic acid ethyl ester, 2-hydroxy-2-methyl ethyl propionate, ethoxy ethyl acetate, hydroxyl ethyl acetate, 2-hydroxy-3-methyl methyl butyrate, 3-methoxy methyl propionate, 3-methoxypropionate, 3-ethoxyl ethyl propionate, 3-ethoxypropanoate, methyl pyruvate, ethyl pyruvate, ethyl acetate, butyl acetate, ethyl lactate, butyl lactate etc.These organic solvents can be used alone, or two or more combinationally uses.
Further, can the high boiling solvent such as glycol monobutyl ether used in combination, glycol monobutyl ether acetic acid esters.In these solvents, propylene glycol monomethyl ether, propylene glycol monomethyl ether, ethyl lactate, butyl lactate and cyclohexanone etc. are preferred for the raising of levelability.
The so-called resist used in the present invention is photoresist, electron sensitive resist.
As the photoresist that the top of the photoetching resist lower membrane in the present invention is coated with, minus, eurymeric can use, and have: the positive light anti-etching agent comprising novolac resin and 1,2-naphthoquinones diazo sulphonic acid ester; Comprise to have and undertaken decomposing by acid and the bonding agent of group making alkali dissolution velocity increase and the chemical amplifying type photoresist of photoacid generator; The low molecular compound comprising alkali-soluble binder, undertaken decomposing by acid and make the alkali dissolution velocity of photoresist increase and the chemical amplifying type photoresist of photoacid generator; Comprise to have and undertaken decomposing by acid and the bonding agent of the group that makes alkali dissolution velocity increase, undertaken decomposing by acid and the chemical amplifying type photoresist of the low molecular compound that makes the alkali dissolution velocity of photoresist increase and photoacid generator; There is in skeleton the photoresist etc. of Si atom, such as ， ロ ー system ア Application ド ハ ー Star society system can be enumerated, trade name APEX-E.
In addition, as the electron sensitive resist that the top of photoetching resist lower membrane is in the present invention coated with, can enumerate and such as comprise main chain and contain Si-Si bond and the composition of the end resin that contains aromatic ring and the acidic acid agent by the irradiation of electron beam, or comprise poly-(4-Vinyl phenol) that hydroxyl be instead of by the organic group containing N-carboxyl amine and pass through the irradiation of electron beam and the composition etc. of acidic acid agent.In the electron sensitive resist composition of the latter, the N-carboxyl aminooxy group of the acid produced by acid agent by electron beam irradiation and polymer lateral chain is reacted, polymer lateral chain resolves into hydroxyl and shows alkali solubility, is dissolved in alkaline-based developer, thus forms Resist patterns.Be somebody's turn to do by the irradiation of electron beam acidic acid agent, can 1 be enumerated, two [rubigan]-2 of 1-, 2,2-trichloroethanes, 1,1-two [p-methoxyphenyl]-2,2, halogenated organic compounds, triphenyl sulfonium salt, the diphenyl iodine such as 2-trichloroethanes, 1,1-two [rubigan]-2,2-ethylene dichloride, the chloro-6-of 2-(trichloromethyl) pyridine salt etc. the sulphonic acid esters such as salt, nitrobenzyl tosylat, dinitrobenzyl tosylate.
The developer solution of the resist of the resist lower membrane formed as having use photoetching resist lower membrane formation composition of the present invention, NaOH can be used, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, the inorganic bases such as ammoniacal liquor, ethamine, the primary amine classes such as n-propylamine, diethylamine, the secondary amine classes such as di-n-butylamine, triethylamine, the tertiary amines such as methyidiethylamine, dimethylethanolamine, the alcaminess such as triethanolamine, Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, the quaternary ammonium salts such as choline, pyrroles, the aqueous solution of the bases such as cyclic amine such as piperidines.In addition, also can add the surfactants such as alcohols, nonionic system such as isopropyl alcohol and use by appropriate amount in the aqueous solution of above-mentioned bases.Wherein, preferred developer solution is quaternary ammonium salt, more preferably Tetramethylammonium hydroxide and choline.
Next Resist patterns formation method of the present invention is described, (such as silicon/silicon dioxide is coated to the substrate used in the manufacture of sophisticated integrated circuits element, glass substrate, the transparency carriers such as ito substrate) on, after carrying out painting erosion resistant agent lower membrane formation composition by the coating process that spinner, coating machine etc. are suitable, carrying out baking makes it solidify, thus makes coating-type underlayer film.Here, as the thickness of resist lower membrane, be preferably 0.01 ~ 3.0 μm.In addition as the condition of baking after coating, for carrying out 0.5 ~ 120 minute at 80 ~ 350 DEG C.Then direct painting erosion resistant agent in resist lower membrane, or as required by 1 layer ~ multilayer film material painting erosion resistant agent again after film forming on coating-type underlayer film, the irradiation of light or electron beam is carried out by the mask of regulation, carry out developing, rinsing, drying, thus good Resist patterns can be obtained.Also heat (PEB:PostExposureBake) after can carrying out the irradiation of light or electron beam as required.Then, by the resist lower membrane of the part eliminating resist of developing is removed by dry ecthing by above-mentioned operation, substrate can form desired pattern.
The exposure light of above-mentioned photoresist, for near ultraviolet ray, far ultraviolet or extreme ultraviolet (such as, EUV, wavelength 13.5nm) etc. chemical ray, such as 248nm (KrF laser), 193nm (ArF laser), 157nm (F can be used 2laser) light of equiwavelength.When illumination is penetrated, as long as by the acidic method of photoacid generator, just can use without particular limitation, exposure is 1 ~ 2000mJ/cm 2, or 10 ~ 1500mJ/cm 2or 50 ~ 1000mJ/cm 2.
In addition the electron beam irradiation of electron sensitive resist can use such as electron beam illuminating device to irradiate.
In the present invention, semiconductor device can be manufactured through following operation: the operation being formed resist lower membrane by resist lower membrane formation composition of the present invention on a semiconductor substrate; This resist lower membrane is formed the operation of resist film; The operation of Resist patterns is formed by light or electron beam irradiation and development; Pass through the operation that formed Resist patterns etches this resist lower membrane; And the operation of processing semiconductor substrate is carried out by the resist lower membrane be patterned.
From now on, if the miniaturization progress of Resist patterns, then can produce the problem of exploring degree, Resist patterns and to collapse after development such problem, thus expect the filming of resist.Therefore, be difficult to obtain and sufficient Resist patterns thickness is processed to substrate, thus need not only to make Resist patterns but also make the resist lower membrane made between resist and the semiconductor substrate that will process also have the technique of the function adding the mask in man-hour as substrate.As the resist lower membrane of such technique, different from existing high etch rates resist lower membrane, require to have the photoetching resist lower membrane of the Selection radio of the dry etching rate close with resist, there is the photoetching resist lower membrane of the Selection radio of the dry etching rate less than resist, there is the photoetching resist lower membrane of the Selection radio of the dry etching rate less than semiconductor substrate.In addition, also can give antireflection ability to such resist lower membrane, the function of antireflection film in the past can be had concurrently.
On the other hand, in order to obtain fine Resist patterns, also bringing into use and making Resist patterns and the resist lower membrane technique thinner than pattern width during resist development when the dry ecthing of resist lower membrane.As the resist lower membrane of such technique, different from high etch rates antireflection film in the past, require the resist lower membrane with the Selection radio of the dry etching rate close with resist.In addition, also can give antireflection ability to such resist lower membrane, the function of antireflection film in the past can be had concurrently.
In the present invention can on substrate after film forming resist lower membrane of the present invention, direct painting erosion resistant agent in resist lower membrane, or as required by 1 layer ~ number coating film material painting erosion resistant agent again after film forming in resist lower membrane.The pattern width of resist narrows thus, even if when in order to prevent pattern collapse to be coated to thinly by resist, and also can by the processing selecting suitable etching gas to carry out substrate.
That is, semiconductor device can be manufactured through following operation: the operation being formed resist lower membrane by resist lower membrane formation composition on a semiconductor substrate; This resist lower membrane is formed the operation of the hard mask obtained by the class coating material containing silicon composition etc. or the hard mask (such as, nitride-monox) obtained by evaporation; Then the operation of resist film is formed on the hard mask; The operation of Resist patterns is formed by the irradiation of light or electron beam and development; Pass through the operation that formed Resist patterns uses halogen system gas to etch to hard mask; By the operation that the hard mask be patterned uses oxygen system gas or hydrogen system gas to etch to this resist lower membrane; And by operation that the resist lower membrane that has been patterned uses halogen system gas to process semiconductor substrate.
When considering the effect of photoetching resist lower membrane formation composition of the present invention as antireflection film, because light absorption position is introduced in skeleton, therefore when heat drying not to the diffusate of photoresist, in addition, because light absorption position has fully large photo absorption performance, therefore prevent the effect of reflected light high.
Photoetching resist lower membrane formation composition of the present invention, thermal stability is high, can prevent the pollution to upper layer film that analyte when burning till causes, and in addition, the temperature allowance of firing process can be made to have enough and to spare.
Further, photoetching resist lower membrane formation composition of the present invention, according to process conditions, can as have prevent light from reflecting function, have and prevent the interaction of substrate and photoresist or prevent the material that uses in photoresist or photoresist is exposed further time the material that generates the film of the function of the ill-effect of substrate is used.
In addition, the present invention also relates to the new compound shown in following formula (5),
(in formula, Q 3represent isopropylidene (-C (CH 3) 2-), R 14the alkyl of the carbon number 2 ~ 10 of the alkyl representing carbon number 2 ~ 10 or the alkoxy with carbon number 1 ~ 10, R 15represent hydrogen atom or methyl, R 13represent the alkyl of carbon number 1 ~ 10 or the aryl of carbon number 6 ~ 40.
N17 represents the integer of 1≤n17≤3, and n18 represents the integer of 1≤n18≤4, and n19 represents the integer of 0≤n19≤3, and n20 represents the integer of 0≤n20≤3, and 2≤(n17+n18+n19+n20)≤5.)。
Abovementioned alkyl, alkoxy, aryl can illustrate above-mentioned illustration.
Embodiment
Synthesis example 1
TMOM-BP (20.00g is added in 100mL eggplant type flask, 0.055mol, Honshu chemical industry (strain) is made, formula (4-23)) and PGME (propylene glycol monomethyl ether, 80.00g) and stir, carrying out heating direct to confirming backflow, making it dissolve to start polymerization.Let cool after 24 hours until 30 DEG C, then obtain TMOM-BP-PGME in PGME solution and (centered by the compound being equivalent to formula (3-4), be mixed with formula (3-1), formula (3-2), the compound shown in formula (3-3).)。Utilize GPC to carry out the qualification that there is ratio of 4 replacement of TMOM-BP-PGME, result is with 34 % by mole of existence in TMOM-BP-PGME entirety.
Synthesis example 2
TMOM-BP (5.00g is added in 200mL eggplant type flask, 0.014mol, Honshu chemical industry (strain) is made, formula (4-23)), as catalyzer spent ion exchange resin through washing 15JWET (20.00g, trade name Amberlist, ダ ウ ケ ミ カ Le society system), PGME (propylene glycol monomethyl ether, 75.00g) stirring, carrying out heating direct to confirming backflow, making it dissolve to start polymerization.Let cool until 60 DEG C after 48 hours, then filtration is carried out to remove 15JWET, filtered by the sediment of gained, the target material obtaining gained (is mixed with formula (3-1), formula (3-2), the compound shown in formula (3-3) centered by the compound being equivalent to formula (3-4).Hereinafter referred to as TMOM-BP-PGME2).
Utilize GPC to carry out the qualification that there is ratio of 4 replacement of TMOM-BP-PGME2, result is with 68 % by mole of existence in TMOM-BP-PGME2 entirety.
Synthesis example 3
TMOM-BP (3.00g is added in 200mL four-hole boiling flask, 0.008mol, Honshu chemical industry (strain) is made, formula (4-23)), as catalyzer spent ion exchange resin through washing 15JWET (12.00g, trade name Amberlist, ダ ウ ケ ミ カ Le society system), add butanols (60.00g, Northeast chemistry (strain) is made) and stir, start polymerization at 100 DEG C.Let cool until 30 DEG C after 48 hours, then 15JWET is filtered, 30 DEG C of concetrated under reduced pressure 2 hours, make it dry, obtain target material and (hereinafter referred to as TBOM-BP-BU, centered by the compound being equivalent to formula (3-8), be mixed with formula (3-5), formula (3-6), the compound shown in formula (3-7).)2.9g。
Pass through 1h-NMR carries out structure elucidation, confirms to obtain target compound.In addition, the ratio that exists being confirmed 4 replacement of TBOM-BP-BU by HPLC is 85 % by mole in TBOM-BP-BU entirety.
The NMR spectrum of 4 replacement of TBOM-BP-BU demonstrates following characteristic absorption (Fig. 1).
1H-NMR(500MHz，DMSO-d6)：0.89ppm(t，12H)，1.36ppm(m，8H)，1.54ppm(m，8H)，3.49(t，8H)，4.54(s，8H)，7.34(s，4H)，8.50(s，2H)。
Synthesis example 4
TM-BIP-A (3.00g is added in 200mL four-hole boiling flask, 0.009mol, Honshu chemical industry (strain) is made, formula (4-24)), as catalyzer spent ion exchange resin through washing 15JWET (12.00g, trade name Amberlist, ダ ウ ケ ミ カ Le society system), add butanols (60.00g, Northeast chemistry (strain) is made) and stir, start polymerization at 100 DEG C.Let cool until 30 DEG C after 3.5 hours, then 15JWET is filtered, 30 DEG C of concetrated under reduced pressure 2 hours, make it dry, obtain target material and (centered by the compound being equivalent to formula (3-12), be mixed with formula (3-9), formula (3-10), the compound shown in formula (3-11).Hereinafter referred to as TBOM-BIP-A) 3.0g.
Pass through 1h-NMR carries out structure elucidation, confirms to obtain target compound.In addition, the ratio that exists being confirmed 4 replacement of TBOM-BIP-A by HPLC is 95 % by mole in TBOM-BIP-A entirety.
The NMR spectrum of 4 replacement of TBOM-BIP-A demonstrates following characteristic absorption (Fig. 2).
1H-NMR(500MHz，DMSO-d6)：0.85ppm(t，12H)，1.30ppm(m，8H)，1.47ppm(m，8H)，1.54ppm(s，6H)，3.38(t，8H)，4.42(s，8H)，6.99(s，4H)，8.19(s，2H)。
Synthesis example 5
TM-BIP-A (4.00g is added in 200mL four-hole boiling flask, 0.011mol, Honshu chemical industry (strain) is made, formula (4-24)), as catalyzer spent ion exchange resin through washing 15JWET (16.00g, trade name Amberlist, ダ ウ ケ ミ カ Le society system), add 1-propyl alcohol (80.00g, Northeast chemistry (strain) is made) and stir, start polymerization at reflux temperature.Let cool until 30 DEG C after 4 hours, then 15JWET is filtered, 30 DEG C of concetrated under reduced pressure 2 hours, make it dry, obtain target material and (centered by the compound being equivalent to formula (3-16), be mixed with formula (3-13), formula (3-14), the compound shown in formula (3-15).Hereinafter referred to as TPOM-BIP-A) 5.0g.
Pass through 1h-NMR carries out structure elucidation, confirms to obtain target compound.In addition, the ratio that exists being confirmed 4 replacement of TPOM-BIP-A by HPLC is 94 % by mole in TPOM-BIP-A entirety.
The NMR spectrum of 4 replacement of TPOM-BIP-A demonstrates following characteristic absorption (Fig. 3).
1H-NMR(500MHz，DMSO-d6)：0.84ppm(t，12H)，1.49ppm(m，8H)，1.55ppm(s，6H)，3.34(t，8H)，4.43(s，8H)，7.00(s，4H)，8.19(s，2H)。
Synthesis example 6
TM-BIP-A (4.00g is added in 200mL four-hole boiling flask, 0.011mol, Honshu chemical industry (strain) is made, formula (4-24)), as catalyzer spent ion exchange resin through washing 15JWET (16.00g, trade name Amberlist, ダ ウ ケ ミ カ Le society system), add ethanol (80.00g, Northeast chemistry (strain) is made) and stir, start polymerization at reflux temperature.Let cool until 30 DEG C after 19.5 hours, then 15JWET is filtered, 30 DEG C of concetrated under reduced pressure 2 hours, make it dry, obtain target material and (centered by the compound being equivalent to formula (3-20), be mixed with formula (3-17), formula (3-18), the compound shown in formula (3-19).Hereinafter referred to as TEOM-BIP-A) 4.2g.
Pass through 1h-NMR carries out structure elucidation, confirms to obtain target compound.In addition, the ratio that exists being confirmed 4 replacement of TEOM-BIP-A by HPLC is 95 % by mole in TEOM-BIP-A entirety.
The NMR spectrum of 4 replacement of TEOM-BIP-A demonstrates following characteristic absorption (Fig. 4).
1H-NMR(500MHz，DMSO-d6)：1.10ppm(t，12H)，1.55ppm(s，6H)，3.44(q，8H)，4.42(s，8H)，6.99(s，4H)，8.22(s，2H)。
Synthesis example 7
TM-BIP-A (4.00g is added in 200mL four-hole boiling flask, 0.011mol, Honshu chemical industry (strain) is made, formula (4-24)), as catalyzer spent ion exchange resin through washing 15JWET (16.00g, trade name Amberlist, ダ ウ ケ ミ カ Le society system), add 2-methyl isophthalic acid-propyl alcohol (80.00g, Northeast chemistry (strain) is made) and stir, start polymerization at 100 DEG C.Let cool until 30 DEG C after 4 hours, then 15JWET is filtered, 30 DEG C of concetrated under reduced pressure 2 hours, make it dry, obtain target material and (centered by the compound being equivalent to formula (3-24), be mixed with formula (3-21), formula (3-22), the compound shown in formula (3-23).Hereinafter referred to as TIBOM-BIP-A) 5.8g.
Pass through 1h-NMR carries out structure elucidation, confirms to obtain target compound.In addition, the ratio that exists being confirmed 4 replacement of TIBOM-BIP-A by HPLC is 95 % by mole in TIBOM-BIP-A entirety.
The NMR spectrum of 4 replacement of TIBOM-BIP-A demonstrates following characteristic absorption (Fig. 5).
1H-NMR(500MHz，DMSO-d6)：0.83ppm(d，24H)，1.55ppm(s，6H)，1.77(m，4H)，3.15(t，8H)，4.44(s，8H)，7.01(s，4H)，8.16(s，2H)。
Synthesis example 8
TM-BIP-A (4.00g is added in 200mL four-hole boiling flask, 0.011mol, Honshu chemical industry (strain) is made, formula (4-24)), as catalyzer spent ion exchange resin through washing 15JWET (16.00g, trade name Amberlist, ダ ウ ケ ミ カ Le society system), add 2-methyl cellosolve (80.00g, Northeast chemistry (strain) is made) and stir, start polymerization at 100 DEG C.Let cool until 30 DEG C after 1 hour, then 15JWET is filtered, 30 DEG C of concetrated under reduced pressure 2 hours, make it dry, obtain target material and (centered by the compound being equivalent to formula (3-28), be mixed with formula (3-25), formula (3-26), the compound shown in formula (3-27).Hereinafter referred to as EGME-BIP-A) 5.3g.
Pass through 1h-NMR carries out structure elucidation, confirms to obtain target compound.In addition, the ratio that exists being confirmed 4 replacement of EGME-BIP-A by HPLC is 94 % by mole in EGME-BIP-A entirety.
The NMR spectrum of 4 replacement of EGME-BIP-A demonstrates following characteristic absorption (Fig. 6).
1H-NMR(500MHz，DMSO-d6)：1.55ppm(s，6H)，3.23ppm(s，12H)，3.44ppm(m，8H)，3.53ppm(m，8H)，4.46(s，8H)，7.01(s，4H)，8.20(s，2H)。
Synthesis example 9
TM-BIP-A (4.00g is added in 200mL four-hole boiling flask, 0.011mol, Honshu chemical industry (strain) is made, formula (4-24)), as catalyzer spent ion exchange resin through washing 15JWET (16.00g, trade name Amberlist, ダ ウ ケ ミ カ Le society system), add cellosolvo (80.00g, Northeast chemistry (strain) is made) and stir, start polymerization at 100 DEG C.Let cool until 30 DEG C after 1 hour, then 15JWET is filtered, 30 DEG C of concetrated under reduced pressure 2 hours, make it dry, obtain target material and (centered by the compound being equivalent to formula (3-32), be mixed with formula (3-29), formula (3-30), the compound shown in formula (3-31).Hereinafter referred to as EGEE-BIP-A) 3.0g.
Pass through 1h-NMR carries out structure elucidation, confirms to obtain target compound.In addition, the ratio that exists being confirmed 4 replacement of EGEE-BIP-A by HPLC is 92 % by mole in EGEE-BIP-A entirety.
The NMR spectrum of 4 replacement of EGEE-BIP-A demonstrates following characteristic absorption (Fig. 7).
1H-NMR(500MHz，DMSO-d6)：1.09ppm(t，12H)，1.55ppm(s，6H)，3.42ppm(m，8H)，3.5ppm(m，16H)，4.46(s，8H)，7.01(s，4H)，8.17(s，2H)。
Synthesis example 10
TM-BIP-A (4.00g is added in 200mL four-hole boiling flask, 0.011mol, Honshu chemical industry (strain) is made, formula (4-24)), as catalyzer spent ion exchange resin through washing 15JWET (16.00g, trade name Amberlist, ダ ウ ケ ミ カ Le society system), add PGME (80.00g, Northeast chemistry (strain) is made) and stir, start polymerization at 100 DEG C.Let cool until 30 DEG C after 1 hour, then 15JWET is filtered, 30 DEG C of concetrated under reduced pressure 2 hours, make it dry, obtain target material and (centered by the compound being equivalent to formula (3-36), be mixed with formula (3-33), formula (3-34), the compound shown in formula (3-35).Hereinafter referred to as PGME-BIP-A) 3.0g.
Pass through 1h-NMR carries out structure elucidation, confirms to obtain target compound.In addition, the ratio that exists being confirmed 4 replacement of PGME-BIP-A by HPLC is 74 % by mole in PGME-BIP-A entirety.
The NMR spectrum of 4 replacement of PGME-BIP-A demonstrates following characteristic absorption (Fig. 8).
1H-NMR(500MHz，DMSO-d6)：1.06ppm(d，12H)，1.55ppm(s，6H)，3.25ppm(s，12H)，3.30ppm(m，8H)，3.63ppm(m，4H)，4.51(q，8H)，7.02(s，4H)，8.07(s，2H)。
Synthesis example 11
TM-BIP-A (4.00g is added in 200mL four-hole boiling flask, 0.011mol, Honshu chemical industry (strain) is made, formula (4-24)), as catalyzer spent ion exchange resin through washing 15JWET (8.00g, trade name Amberlist, ダ ウ ケ ミ カ Le society system), add ethylene glycol isopropyl ether (80.00g, Northeast chemistry (strain) is made) and stir, start polymerization at 40 DEG C.Heating direct to 70 DEG C after 22 hours, react 12 hours, after letting cool, 15JWET is filtered, 30 DEG C of concetrated under reduced pressure 2 hours, make it dry, obtain target material and (centered by the compound being equivalent to formula (3-40), be mixed with formula (3-37), formula (3-38), the compound shown in formula (3-39).Hereinafter referred to as EGIPE-BIP-A) 3.0g.
Pass through 1h-NMR carries out structure elucidation, confirms to obtain target compound.In addition, the ratio that exists being confirmed 4 replacement of EGIPE-BIP-A by HPLC is 84 % by mole in EGIPE-BIP-A entirety.
The NMR spectrum of 4 replacement of EGIPE-BIP-A demonstrates following characteristic absorption (Fig. 9).
1H-NMR(500MHz，DMSO-d6)：1.07ppm(t，24H)，1.55ppm(s，6H)，3.45-3.57ppm(m，20H)，4.47(s，8H)，7.00(s，4H)，8.14(s，2H)。
Synthesis example 12
N-phenyl-1-naphthylamine (10.00g is added in 100mL four-hole boiling flask, 0.046mol, Tokyo change into industry (strain) system), 1-naphthaldehyde (7.12g, 0.046mol, Tokyo changes into industry (strain) system), p-toluenesulfonic acid monohydrate (0.908g, 0.0046mol, Northeast chemistry (strain) make), add Isosorbide-5-Nitrae-two alkane (21.03g, Northeast chemistry (strain) is made) also stirs, heating direct to 110 DEG C, makes it dissolve, starts polymerization.Let cool after 12 hours until room temperature, then in methyl alcohol (400g, Northeast chemistry (strain) is made), make it precipitate again.The sediment of gained is filtered, utilizes pressure Reduction Dryer 50 DEG C of dryings 10 hours, further 120 DEG C of dryings 24 hours, obtain subject polymer (being equivalent to formula (5-1)), hereinafter referred to as pNPNA-NA) 11.6g.PNPNA-NA by GPC obtain with polystyrene conversion measure weight-average molecular weight Mw for 1400, polydispersity Mw/Mn is 1.62.
Embodiment 1
The TMOM-BP-PGME of 0.10g as the synthesis example 1 of crosslinking chemical, the pPTS (pyridine as catalyzer is mixed in the pNPNA-NA resin 0.51g obtained by synthesis example 12 tosilate) 0.02g, メ ガ Off ァ ッ Network R-30N (large Japanese イ Application キ chemistry (strain) system as surfactant, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Embodiment 2
0.10g is mixed as the TMOM-BP-PGME2 of the synthesis example 2 of crosslinking chemical, the pPTS0.02g as catalyzer, (large Japanese イ Application キ chemistry (strain) system of the メ ガ Off ァ ッ Network R-30N as surfactant in the pNPNA-NA resin 0.51g obtained by synthesis example 12, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Embodiment 3
0.10g is mixed as the TBOM-BP-BU of the synthesis example 3 of crosslinking chemical, the pPTS0.02g as catalyzer, (large Japanese イ Application キ chemistry (strain) system of the メ ガ Off ァ ッ Network R-30N as surfactant in the pNPNA-NA resin 0.51g obtained by synthesis example 12, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Embodiment 4
0.10g is mixed as the TBOM-BIP-A of the synthesis example 4 of crosslinking chemical, the pPTS0.02g as catalyzer, (large Japanese イ Application キ chemistry (strain) system of the メ ガ Off ァ ッ Network R-30N as surfactant in the pNPNA-NA resin 0.51g obtained by synthesis example 12, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Embodiment 5
0.10g is mixed as the TPOM-BIP-A of the synthesis example 5 of crosslinking chemical, the pPTS0.02g as catalyzer, (large Japanese イ Application キ chemistry (strain) system of the メ ガ Off ァ ッ Network R-30N as surfactant in the pNPNA-NA resin 0.51g obtained by synthesis example 12, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Embodiment 6
0.10g is mixed as the TEOM-BIP-A of the synthesis example 6 of crosslinking chemical, the pPTS0.02g as catalyzer, (large Japanese イ Application キ chemistry (strain) system of the メ ガ Off ァ ッ Network R-30N as surfactant in the pNPNA-NA resin 0.51g obtained by synthesis example 12, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Embodiment 7
0.10g is mixed as the TIBOM-BIP-A of the synthesis example 7 of crosslinking chemical, the pPTS0.02g as catalyzer, (large Japanese イ Application キ chemistry (strain) system of the メ ガ Off ァ ッ Network R-30N as surfactant in the pNPNA-NA resin 0.51g obtained by synthesis example 12, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Embodiment 8
0.10g is mixed as the EGME-BIP-A of the synthesis example 8 of crosslinking chemical, the pPTS0.02g as catalyzer, (large Japanese イ Application キ chemistry (strain) system of the メ ガ Off ァ ッ Network R-30N as surfactant in the pNPNA-NA resin 0.51g obtained by synthesis example 12, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Embodiment 9
0.10g is mixed as the EGEE-BIP-A of the synthesis example 9 of crosslinking chemical, the pPTS0.02g as catalyzer, (large Japanese イ Application キ chemistry (strain) system of the メ ガ Off ァ ッ Network R-30N as surfactant in the pNPNA-NA resin 0.51g obtained by synthesis example 12, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Embodiment 10
0.10g is mixed as the PGME-BIP-A of the synthesis example 10 of crosslinking chemical, the pPTS0.02g as catalyzer, (large Japanese イ Application キ chemistry (strain) system of the メ ガ Off ァ ッ Network R-30N as surfactant in the pNPNA-NA resin 0.51g obtained by synthesis example 12, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Embodiment 11
0.10g is mixed as the EGIPE-BIP-A of the synthesis example 11 of crosslinking chemical, the pPTS0.02g as catalyzer, (large Japanese イ Application キ chemistry (strain) system of the メ ガ Off ァ ッ Network R-30N as surfactant in the pNPNA-NA resin 0.51g obtained by synthesis example 12, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Comparative example 1
TMOM-BP (Honshu chemical industry (strain) system of 0.10g as crosslinking chemical is mixed in the pNPNA-NA resin 0.51g obtained by synthesis example 12, formula (4-23)), the pPTS0.02g as catalyzer, the メ ガ Off ァ ッ Network R-30N as surfactant (large Japanese イ Application キ chemistry (strain) system, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Comparative example 2
TM-BIP-A (Honshu chemical industry (strain) system of 0.10g as crosslinking chemical is mixed in the pNPNA-NA resin 0.51g obtained by synthesis example 12, formula (4-24)), the pPTS0.02g as catalyzer, the メ ガ Off ァ ッ Network R-30N as surfactant (large Japanese イ Application キ chemistry (strain) system, trade name) 0.001g, be dissolved in PGMEA (propylene glycol monomethyl ether) 7.16g, PGME1.52g and cyclohexanone 2.39g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Comparative example 3
The tetramethoxymethylglycoluril of 0.10g as crosslinking chemical, the pPTS of the 0.02g as catalyzer, メ ガ Off ァ ッ Network R-30N (large Japanese イ Application キ chemistry (strain) system as surfactant is mixed in the pNPNA-NA resin 0.51g obtained by synthesis example 12, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
Comparative example 4
0.10g is mixed as four butoxymethyl glycolurils of crosslinking chemical, the pPTS as the 0.02g of catalyzer, the メ ガ Off ァ ッ Network R-30N as surfactant (large Japanese イ Application キ chemistry (strain) system in the pNPNA-NA resin 0.51g obtained by synthesis example 12, trade name) 0.001g, be dissolved in the cyclohexanone of the PGMEA (propylene glycol monomethyl ether) of 7.16g, PGME and 2.39g of 1.52g, make solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the solution utilizing the resist lower membrane formation composition used in the photoetching process of multilayer film.
(mensuration of sublimate amount)
The mensuration of sublimate amount uses the sublimate amount determining device of No. 2007/111147th, International Publication described in pamphlet to implement.First, on the silicon wafer substrate of diameter 4 inches, utilize spin coater to be coated with the resist lower membrane of being modulated by embodiment 1 ~ embodiment 11, comparative example 1 ~ comparative example 4 and formed with composition to make thickness for 100nm.The wafer being coated with resist lower membrane is positioned over the above-mentioned sublimate amount determining device of electric hot plate integration, toast 120 seconds, by sublimate trapping to QCM (QuartzCrystalMicrobalance) sensor, be namely formed with the quartz crystal unit of electrode.If qcm sensor can utilize adhere to sublimate on the surface (electrode) of quartz crystal unit, the character of the frequency change (decline) of quartz crystal unit according to its quality, measure the mass change of trace.
Detailed determination step is as follows.The electric hot plate of sublimate amount determining device is warming up to the mensuration temperature described in table 1, pump discharge is set as 1m 3/ s, places in order to device stabilization for initial 60 seconds.Then immediately the wafer being coated with resist lower membrane is promptly placed in electric hot plate from slip mouth, carries out the trapping from the moment of 60 seconds to the sublimate in the moment (120 seconds) of 180 seconds.In addition, nozzle is not installed use as flow-through attachments (flowattachment) (detecting portion) of connection of qcm sensor with trapping funnel part at above-mentioned sublimate amount determining device, therefore, from the stream (bore: 32mm) that the distance with sensor (quartz crystal unit) is the chamber unit of 30mm, air-flow is not flowed into by concentrating.In addition, qcm sensor employs and uses the material (AlSi) of Silicified breccias as major component as electrode, the diameter (sensor diameter) of quartz crystal unit is 14mm, and the electrode diameter on quartz crystal unit surface is 5mm, and resonant frequency is the qcm sensor of 9MHz.
The frequency change of gained to be converted into gram according to measuring the eigenvalue of quartz crystal unit used, to make the relation of the sublimate amount of the wafer 1 being coated with resist lower membrane and time process clear and definite.In addition, within initial 60 seconds, placing (not arranging wafer) time-bands in order to device stabilization, is the measured value relevant to the sublimate amount of wafer from the measured value in the moment of 60 seconds to the moment of 180 seconds wafer being placed in electric hot plate.Sublimate amount by the quantitative resist lower membrane of this device is shown in Table 1 in the mode of sublimate amount ratio.In addition, 2000ng as the upper limit, if be below 2000ng, is defined as good, if be more than 2000ng, is defined as bad by sublimate amount.The situation of below 2000ng is represented with zero, the situation of more than 2000ng with × represent.
[table 1]
Table 1: the sublimate amount produced by resist lower membrane
(dissolution test in photoresist solvent)
Use spin coater, the resist lower membrane of being modulated by embodiment 1 ~ 11 and comparative example 1 ~ 4 is formed and coats respectively on silicon wafer with the solution of composition.Electric hot plate burns till 2 minutes at 400 DEG C, forms resist lower membrane (thickness 0.25 μm).This resist lower membrane be impregnated in the solvent that resist uses, such as ethyl lactate and propylene glycol monomethyl ether, propylene glycol monomethyl ether, cyclohexanone, confirm in these solvents insoluble.
(imbedibility of sectional hole patterns is tested)
Whether the resist lower membrane by above-mentioned acquisition is formed can to imbed in hole well with composition and evaluates.By spin coater, painting erosion resistant agent lower membrane formation on tetraethyl orthosilicate (TEOS) substrate forming porose (bore dia: 0.120nm, spacing: between bore dia/hole ratio=1/0.8 at interval, the degree of depth in hole: 400nm).Then, 240 DEG C of heating 1 minute on electric hot plate, be about 120nm using thickness and form resist lower membrane (situation as the purposes of photoetching gap-fill material).By using scanning electron microscope (SEM), observing the cross sectional shape with the TEOS substrate in hole being coated with the resist lower membrane formation obtained by embodiment 1 ~ 11 and comparative example 1 ~ 4, thus evaluating imbedibility.Regard resist lower membrane very close to each other situation about being formed in hole as imbedibility good ("○"), by imbed at Kong Zhongwei or in hole, there is hole, the situation in gap is set to bad ("×").
[table 2]
Table 2: the imbedibility of resist lower membrane
Industry utilizability
The photoetching process employing crosslinking chemical of the present invention resist lower membrane formation composition used is different from the material being difficult to have concurrently the imbedibility suppressing low by the generation of sublimate and in sectional hole patterns in the past, can provide the resist lower membrane having these two characteristics concurrently.

Claims (16)

1. a resist lower membrane formation composition, it comprises resin and following formula (1) or the cross-linked compound shown in formula (2),
In formula, Q 1represent the organic group of singly-bound or m1 valency, R 1and R 4the alkyl of the carbon number 2 ~ 10 of the alkyl representing carbon number 2 ~ 10 respectively or the alkoxy with carbon number 1 ~ 10, R 2and R 5represent hydrogen atom or methyl respectively, R 3and R 6represent the alkyl of carbon number 1 ~ 10 or the aryl of carbon number 6 ~ 40 respectively,
N1 represents the integer of 1≤n1≤3, and n2 represents the integer of 2≤n2≤5, and n3 represents the integer of 0≤n3≤3, and n4 represents the integer of 0≤n4≤3, and 3≤(n1+n2+n3+n4)≤6,
N5 represents the integer of 1≤n5≤3, and n6 represents the integer of 1≤n6≤4, and n7 represents the integer of 0≤n7≤3, and n8 represents the integer of 0≤n8≤3, and 2≤(n5+n6+n7+n8)≤5, m1 represent the integer of 2 ~ 10.
2. resist lower membrane formation composition according to claim 1, Q 1for singly-bound, or for being selected from the organic group of the m1 valency in the chain alkyl of carbon number 1 ~ 10, the aromatic series base of carbon number 6 ~ 40 or their combination.
3. resist lower membrane formation composition according to claim 1 and 2, described formula (1) or the cross-linked compound shown in formula (2) are by the compound shown in following formula (3) or formula (4), obtain with the reaction containing the ether compound of hydroxyl or the alcohol of carbon number 2 ~ 10
In formula, Q 2represent the organic group of singly-bound or m2 valency, R 8, R 9, R 11and R 12represent hydrogen atom or methyl respectively, R 7and R 10represent the alkyl of carbon number 1 ~ 10 or the aryl of carbon number 6 ~ 40 respectively,
N9 represents the integer of 1≤n9≤3, and n10 represents the integer of 2≤n10≤5, and n11 represents the integer of 0≤n11≤3, and n12 represents the integer of 0≤n12≤3, and 3≤(n9+n10+n11+n12)≤6,
N13 represents the integer of 1≤n13≤3, and n14 represents the integer of 1≤n14≤4, and n15 represents the integer of 0≤n15≤3, and n16 represents the integer of 0≤n16≤3, and 2≤(n13+n14+n15+n16)≤5, m2 represent the integer of 2 ~ 10.
4. resist lower membrane formation composition according to claim 3, following formula (3) or the compound shown in formula (4), carries out in the presence of acid catalyst with the reaction containing the ether compound of hydroxyl or the alcohol of carbon number 2 ~ 10.
5. resist lower membrane formation composition according to claim 4, acid catalyst is catalyzer spent ion exchange resin.
6. resist lower membrane formation composition according to any one of claim 3 to 5, the ether compound containing hydroxyl is propylene glycol monomethyl ether or propylene glycol monoethyl.
7. resist lower membrane formation composition according to any one of claim 3 to 5, the alcohol of carbon number 2 ~ 10 is ethanol, 1-propyl alcohol, 2-methyl isophthalic acid-propyl alcohol, butanols, 2-methyl cellosolve or cellosolvo.
8. the resist lower membrane formation composition according to any one of claim 1 ~ 7, resin is novolac resin.
9. the resist lower membrane formation composition according to any one of claim 1 ~ 8, it comprises crosslinking chemical further.
10. the resist lower membrane formation composition according to any one of claim 1 ~ 9, it comprises acid and/or acid agent further.
11. 1 kinds of resist lower membrane, it is undertaken burning till obtaining by being coated on semiconductor substrate by the resist lower membrane formation composition described in any one of claim 1 ~ 10.
12. 1 kinds of formation methods for the manufacture of the Resist patterns of semiconductor, it comprises following operation: coated by the resist lower membrane formation composition described in any one of claim 1 ~ 10 and semiconductor substrate carries out burning till and forms the operation of resist lower membrane.
The manufacture method of 13. 1 kinds of semiconductor devices, it comprises following operation: the operation being formed resist lower membrane by the resist lower membrane formation composition described in any one of claim 1 ~ 10 on a semiconductor substrate; This resist lower membrane is formed the operation of resist film; The operation of Resist patterns is formed by the irradiation of light or electron beam and development; Pass through the operation that formed Resist patterns etches this resist lower membrane; And the operation of processing semiconductor substrate is carried out by the resist lower membrane be patterned.
The manufacture method of 14. 1 kinds of semiconductor devices, it comprises following operation: the operation being formed resist lower membrane by the resist lower membrane formation composition described in any one of claim 1 ~ 10 on a semiconductor substrate; This resist lower membrane is formed the operation of hard mask; Form the operation of resist film further on the hard mask; The operation of Resist patterns is formed by the irradiation of light or electron beam and development; Pass through the operation that formed Resist patterns carrys out etch hard mask; The operation of this resist lower membrane is etched by the hard mask be patterned; And the operation of processing semiconductor substrate is carried out by the resist lower membrane be patterned.
15. manufacture methods according to claim 14, hard mask is formed by the coating of inorganics or the evaporation of inorganics.
Compound shown in 16. following formula (5),
In formula, Q 3represent isopropylidene, R 14the alkyl of the carbon number 2 ~ 10 of the alkyl representing carbon number 2 ~ 10 or the alkoxy with carbon number 1 ~ 10, R 15represent hydrogen atom or methyl, R 13represent the alkyl of carbon number 1 ~ 10 or the aryl of carbon number 6 ~ 40,
N17 represents the integer of 1≤n17≤3, and n18 represents the integer of 1≤n18≤4, and n19 represents the integer of 0≤n19≤3, and n20 represents the integer of 0≤n20≤3, and 2≤(n17+n18+n19+n20)≤5.
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